Winfrey draws rich and famous to Obama bash at California estate

Christi Parsons and John McCormickTribune staff reporters

Helicopters carrying camera crews buzzed overhead, and tinted glass covered the windows of almost every vehicle entering as Oprah Winfrey welcomed 1,500 guests Saturday evening to her sprawling estate in what was the biggest fundraiser of Sen. Barack Obama's political career.

Obama bumped elbows with comedians Chris Rock and Whoopi Goldberg. Singer Stevie Wonder an Obama favorite, performed.But it was the joint appearance by Obama and Winfrey, who never before has involved herself in politics in such a large way, that generated the greatest star power of the evening.

"I call my home the Promised Land because I get to live Dr. King's dream," Winfrey told her guests, a source inside recalled Winfrey saying. "I haven't been actively engaged before because there hasn't been anything to be actively engaged in. But I am engaged now to make Barack Obama the next president of the United States."

The star-studded gathering marked the most visible effort yet for the billionaire media magnate in her effort to help the Illinois Democrat in his quest to win his party's presidential nomination.

As Winfrey introduced Obama's wife, Michelle, who was wearing a dress by Chicago designer Maria Pinto, the hostess called her the "first lady."

At times, Winfrey echoed Obama's stump speech. "How many hours you have spent in the halls of Washington is not the issue," she said, according to the source. "I want a man that has good sense."

Winfrey said she never expected to be involved in a presidential campaign. "When you have been called, no one can stand in the way of destiny," she reportedly said.

Once inside, guests, who dined on mini-hamburgers, chicken tenders and corn on the cob, had various levels of access, ranging from seats in the grass on lime-green blankets that had "Obama '08" embroidered on them, to a VIP reception, to a later, much more exclusive dinner.

Smartly timed with Monday's season premiere of Winfrey's show, the event was part fundraiser, part Hollywood red carpet and part circus. Photographers hovered outside entrances of Winfrey's 42-acre property, where VIP guests were allowed to drive right in. Others had to park and ride from a horse-show grounds in nearby Santa Barbara. Journalists were kept outside.

At the grounds, guests parked, had their possessions searched and boarded buses for the trip to Winfrey's property about 8 miles away. Recording devices and cameras were not allowed, and government-issued photo IDs were compared to a guest list.

The power of Oprah

In an interview Friday, Obama said he first fully realized Winfrey's power one day when he was running late for work at the Capitol and a beefy security guard in dark sunglasses stopped his car and peered in sternly to ask for identification.

Suddenly, though, the Senate ID wasn't necessary for the freshman lawmaker. "Hey, you were on 'Oprah'!" the man said, stepping back to direct Obama's car through the checkpoint with a friendly wave.

"It's at that point that I realized the power of Oprah Winfrey," Obama recalled. "Her reach extended beyond the stereotypical demographic. ... And the appearance on her show amplified my profile around the country."

At that time, Obama was several months past the 2004 Democratic National Convention speech that had made him a political star, and his first published memoir was selling well.

But an appearance on "The Oprah Winfrey Show" had widened his path into the world of pop culture, a critical domain as he began to build his celebrity-infused political portfolio. The relationship has grown along with Obama's rise, as the two Chicago celebrities have turned a passing acquaintance into a powerful friendship with national implications.

Saturday's gathering was expected to raise more than $3 million. And it may be only the beginning of her support, with television ads featuring Winfrey and even speaking appearances possible.

It is not a simple prospect for any star, especially for one who so jealously guards her brand identity. In joining Obama's campaign, Winfrey is flouting the lessons of celebrities who have closely associated themselves with candidates, only to turn off a certain segment of their audiences and diminish their own marketability.

She's also testing the boundaries of her power. Winfrey has turned obscure writers into best sellers and started a top magazine from scratch, yet she never before has tried so tangibly to translate her influence into the political realm.

Some suggest that if any star is well-established enough to risk it, it is Winfrey. She is especially popular with women and African-Americans, crucial demographics for Obama as he competes against front-runner Sen. Hillary Clinton (D-N.Y.), who enjoys solid support from both those groups.

"As a marketer, [Winfrey's] power lies in being able to make her recommendations seem very friendly, like they are coming from a girlfriend," said Kathleen Rooney, who is updating a 2005 book about the influence of Winfrey's book club.

Or, as Winfrey recently told Larry King, "My support of him is probably worth more than any check that I could write."

So when she expressed interest in helping Obama, his staff was more than happy to start the discussions. They didn't need a recent Gallup Poll to tell them Winfrey is one of the most influential women in America. (She ranked second in the most recent poll to Clinton.)

Winfrey, who declined an interview request, has become good friends with Obama and his wife in the past couple of years.

They didn't really know each other well until the fall of 2004, when Winfrey, inspired by Obama's national convention address, asked to interview the Obamas for her magazine. She visited their house and, as is evident from the laughter and warm chatter in the recording of their conversation, the three hit it off right away.

After that interview, say people who know them, Winfrey and the Obamas became social friends, with the couple even visiting her Chicago home. Later, Winfrey and the senator flew together from Chicago to view the devastation of Hurricane Katrina and displaced Gulf Coast residents.

Just months after Obama's Senate term began, a confidant says, Obama told friends about a visit he and his wife paid to Winfrey's California home as part of her Legends Ball weekend honoring African-American women.

The group included music legend Quincy Jones, and it was on that May 2005 visit to Winfrey's Montecito estate that the idea of Winfrey hosting a political event apparently came up.

Obama has said he was not actively planning a White House run at the time, but it may have been something Winfrey was contemplating for him.

"'Wouldn't this be a great place for a fundraiser?' I said jokingly," Winfrey recalled of the gathering that weekend during a recent interview on her satellite radio channel.

The glitz that weekend was nothing compared to what transpired Saturday on Winfrey's property, which features a man-made lake and a 23,000-square-foot mansion that is located between the ocean and mountains.

One of Obama's top national fundraisers said more than one high-wattage guest cut short a European vacation to be here.

Because so many celebrities and wealthy donors have already given the maximum allowed by federal law, the California fundraiser said many needed to raise money from smaller donors in order to get a ticket.

"It's hard to find people who haven't given to him," the fundraiser said, speaking on condition of anonymity for fear of angering Obama or Winfrey.

Others are doubling down, giving to two or more candidates. Actor Tom Hanks, for example, already has given the maximum allowed to Obama and Clinton. Ben Stiller, meanwhile, has given to those two, as well as to former North Carolina Sen. John Edwards.

While the scene was flashy even by Hollywood standards, the attire Saturday was fairly casual, with women wearing summer dresses and many men in sport coats.

Calling her estate a "special, sacred, spiritual" place, Winfrey had warned her guests to be on their best behavior. "To offer it ... is no small thing for me," she said. "There are going to be some serious restrictions and requirements to get in here."

She wasn't kidding. Visitors were instructed to wear flat shoes and other "garden attire," because the event mostly took place in a meadow on the property.

Only approved photographers were allowed inside, and organizers had searched the guest list to try to make sure no paparazzi snuck in by paying the $2,300 admission.

Students of the Oprah phenomenon say Winfrey has an almost obsessive protectiveness, not just of her home but also her image and brand. Some are skeptical of just how much her endorsement will help Obama in early-voting states where his fate likely will be decided.

Obama agrees it is difficult to predict how much Winfrey's backing will help.

"It's very hard to say," he said. "I think a presidential race is unique. The job is unique. People who might buy my book because of an appearance on Oprah are obviously going to have a much more serious and sober deliberation when it comes to deciding who the next leader of the free world is."

Still, he said, he has no doubt that Winfrey's support will help him, at the very least, to reach voters who might not otherwise hear what he has to say.

"Ultimately, they've got to be persuaded by me that I'm the right person for the job," Obama said, but "Oprah is somebody who has enormous reach, and that means that I may get a hearing in certain quarters."